Twenty Years High: Bobby Black’s 40 Most Infamous Moments

While High Times celebrates its 40th anniversary this year, 2014 also marks a more personal milestone for me — my 20th year with the magazine. Having worked at the world’s most notorious magazine for half of its existence has afforded me some truly incredible opportunities and experiences. To commemorate these amazing anniversaries, I thought I’d share with you my 40 most infamous career moments from the past two decades. I hope you enjoy this brief jaunt down memory lane.

1. Smoking out with Snoop Dogg.

An epic staff session at our old offices back in 2000.

2. Addressing the 40,000 attendees of the Denver 4/20 Rally in 2012.

3.Walking the red carpet at the 2006 AVN awards.
Going to the Oscars of porn with a plethora of Penthouse Pets by my side—including Pet of the Year Jamie Lynn—was one of the most exciting nights of my life.Watch the video.Read the article.

5.Getting engaged at the 19th Cannabis Cup in Amsterdam.
I’d met the love of my life April at the Cup two years earlier. This time, I popped the question during a romantic canal cruise.

6.Working the “green carpet” at the 10th annual Stony Awards in Hollywood.
Got a chance to interview Cheech & Chong, Craig Robinson and many other celebs.Watch the video.Read the article.

7.Smoking a bowl with Ozzy Osbourne. At the photo shoot for our March 1999 cover, having helped interview Ozzy and Tony Iommi the day before. Truly legendary.Read the article.

8.Presenting Doobie Awards to Cypress Hill and Slightly Stoopid onstage at the Red Rocks Amphitheater.
It was at the 2013 Denver Cannabis Cup VIP party. The energy from the crowd was thrilling.Watch the video.Read the article.

9.Visiting the set of Harold & Kumar Escape From Guantanamo Bay.
Got to interview stars John Cho and Kal Penn and watch them film the scene where Kumar gets high for the first time.Watch the video.Read the article.

10.Presenting the HT Lifetime Achievement Award for music to Johnny Winter onstage at Irving Plaza.
One of the greatest blues guitarists of all time, whom I’d gone to see for my very first concert with my dad.Watch the video.Read the article.

11.Meeting Tony Clifton at the 2012 Doobie Awards in Austin.
Becoming buddies with Andy Kaufman’s greatest creation was an unexpected honor.Watch the video.Read the article.

12.Escorting George Clinton around the 2010 Detroit Medical Cannabis Cup.
The king of funk was stoked to be there and as jolly as can be.Watch the video.

13. Filming a scene for the movie Pot Luck with Jackie “The Joke Man” Martling.
Being an extra in HT’s first foray into film was a ton of fun.Watch the video.Read the article.

14.Ron Jeremy falling asleep during our interview at AVN 2006.
He was super-nice, but it was the end of a very busy convention and he was understandably exhausted.Read the article.

15. My bachelor party roast.
At NYC’s Delancey club in August 2011. I got dissed hard by comedian Rob Cantrell, Sirius personality Jose Mangin and others, then dished it right back.Read the article.

16. Getting arrested in Amsterdam.
Spent an hour in a Dutch jail for handing out weed on the street at the 2006 Cannabis Cup. Oops … my bad.

17. Watching Metallica perform live at The Colbert Report.
I was escorted in by my buddy Jason, who works on the show. Intimately epic.Watch the video.

18. Posing in an alien mask for our cover.
For the August 1995 UFO issue. Take me to your dealer!Watch the video.Read the article.

19.Smoking from a porn star’s vagina live on the Howard Stern show.
I accompanied Jen Steele and Miss High Times 2006 to the show and ended up getting interviewed by Howard. Pretty awesome.Watch the video.Read the article.

20.Acting as a celebrity judge for the US Air Guitar competition.
Served alongside The Daily Show’s Jason Jones and Andrew W.K. at NYC’s Bowery Ballroom.Watch the videos here and here.Read the article.

21.Running for president.
A mock campaign to promote “Smoke the Vote” that included a nationwide tour and a debate with rival candidate Pakelika (RIP) from the Kottonmouth Kings.Watch the videos here and here.Read the articles.

22. Smoking a vapor pen live on the Fox News Channel with Geraldo Rivera.
I was as surprised as you are (though, sadly, it was nicotine oil, not cannabis).Watch the video.Read the article.

23.Seeing my face tattooed on a fan at the 2008 Cannabis Cup.
I knew there were some hardcore Blackolytes out there, but wow.Read the article.

24. Interviewing Pantera’s Phil Anselmo.
Backstage at NYC’s Best Buy Theater in 2011. One of the best interviews of my career.Watch the videos.Read the article.

25. Meeting Rush at Newark’s Prudential Center.
Got my album signed and a photo with Geddy and Alex.Read the article.

26.Playing pool with Jerry Cantrell of Alice in Chains.
At a SXSW stoner rock showcase at a bar in Austin, in March 2002.Read the article.

27.Going on tour with Sepultura for three days in 1996.
It was my first trip as a young HIGH TIMES journalist. I got to ride on their tour bus and watch the show from the stage.

28. Blazing with Jenna Jameson in a NYC strip club.
The former porn queen was far more down to earth than I’d expected.Read the article.

29.The 2006 Ganja Goddess party at Headquarters gentleman’s club in NYC.
An open bar, a slew of strippers and Penthouse Pets … and Redman!See the gallery.

30. Art directing Tera Patrick’s cover/centerfold shoot.
The world’s hottest porn star, naked on a bed full of buds in a party suite at the Palms Hotel in Las Vegas.Watch the video.Read the article.

32. Monster Magnet performing for the inaugural episode of Contact High.
Live in the studios of Sirius Satellite Radio for my former stoner rock show.

33. Running the Miss High Times pageant in Jamaica (2007-2008).
Buds and babes on the beaches of Negril!Read the article:http://www.hightimes.com/read/party-ganja-beach34. Interviewing Robby Krieger of The Doors.
A living legend — one of my life’s greatest honors.Read the article.

35. The release of High Volume: The Stoner Rock Collection.
A compilation album that I organized, produced and art-directed for HT Records. Among my proudest achievements.Read the article.Hear/buy the album here.